Propargylation of Ugi Amide Dianion: An Entry into Pyrrolidinone and Benzoindolizidine Alkaloid Analogues
| Autor: | Nour E. A. Abd El-Sattar, Alaa Zidan, Ali Khalil Ali, Marie Cordier, Abeer M. El-Naggar, Mohamed A. Hassan, Laurent El Kaim |
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| Přispěvatelé: | Laboratoire de synthèse organique (DCSO), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Faculty of Science [ASU], Ain Shams University (ASU), Laboratoire de chimie moléculaire (LCM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-École polytechnique (X), École Nationale Supérieure de Techniques Avancées (ENSTA Paris) |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Chemistry Hydride [CHIM.ORGA]Chemical Sciences/Organic chemistry Alkaloid Organic Chemistry Iminium 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences 3. Good health Adduct chemistry.chemical_compound Nucleophile Amide Physical and Theoretical Chemistry Excess sodium |
| Zdroj: | Organic Letters Organic Letters, American Chemical Society, 2018, 20 (9), pp.2568-2571. ⟨10.1021/acs.orglett.8b00687⟩ |
| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/acs.orglett.8b00687⟩ |
| Popis: | International audience; Propargylation of Ugi adducts under the addition of excess sodium hydride in DMSO leads to direct formation of pyrrolidinone enamides, which are useful precursors of iminium intermediates and may be trapped by various nucleophiles. This approach has been applied to the formation of benzoindolizidine alkaloids with high diversity via a Ugi/propargylation/Pictet-Spengler cyclization. |
| Databáze: | OpenAIRE |
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